Hipsters & Lace
by raehex
Summary: He stood there, hands on his hips, his fingers grazing just beneath the elastic, and had to admit… it had been a while since he had worn anything this damn skimpy. Sure, he'd wrestled in trunks before, and very tiny ones at that sometimes, but this was a new level for him. [Dean/OC. Rated M for crossdressing and smut.]


**A/N**: This was written as a gift for SpaMightWrite over on AO3, and was actually a commissioned fic. I had far too much fun with this!

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><p>"What did I tell you about stealing my clothes?"<p>

Em grumbled, hiding her face in the hood of his sweatshirt. She slept better wearing his clothes. She didn't know why but it just was a thing she had discovered one night when she was home alone, which resulted in her now almost always stealing his clothes. A t-shirt when she would run downstairs to the kitchen, a hoodie when she couldn't sleep, boxers because she _just wanted to._ It was comforting, wearing his clothes, and she thought she looked cute too.

"Em, answer me."

"Mmf." She burrowed her face back into her pillow, not wanting to really wake up to get fussed at about his clothes. It's not like _wore_ most of these, he stayed relegated to the same crappy five t-shirts and two jackets. Besides, he mainly wore the compression underwear since he was wrestling about 95% of his life, who cared if she wore his tacky ass Walmart boxers?

"I'm fucking talking to you!" He finally grabbed the hood of the hoodie from the back of her head, pulling until she felt the cold of the air hit her face. He was being overwhelmingly obnoxious today, more so than usual.

"Alright, what's the big fucking deal…" Her argument died in her throat as she rolled over.

Because right in her face was Dean's crotch. Covered in underwear that was _overwhelmingly not his_.

"Are you wearing my underwear?!"

He shrugged, turning around as if to look at himself. They were brightly colored hipsters, red and blue horizontal stripes separated by tiny yellow pinstripes, with a little yellow bow at the front, right beneath the elastic waist. The colors looked great against his skin, but she was more stuck on the image of his cock straining against the fabric, the head just poking from above the waist.

"What, don't like your clothes being taken?"

"I don't stretch out your shit though."

"Fuck you, I'm not stretching out your goddamn panties."

"Your cock begs to differ."

"Well, maybe my cock wants to look pretty."

"You're insane."

"You love it."

He stood there, hands on his hips, his fingers grazing just beneath the elastic, and had to admit… it had been a while since he had worn anything _this_ damn skimpy. Sure, he'd wrestled in trunks before, and very tiny ones at that sometimes, but this was a new level for him.

"No, but like… does it look good?" The tension was obvious in his voice, anxiety tinting the edges of his words. He nervously drummed fingers against his hip, looking at her, chewing slowly at his chapped bottom lip. Sure, this may have been a little prank, just to get a rise out of her, but he wanted to make sure he didn't look stupid doing it.

Em took the moment to actually appreciate the view in front of her. It was a strange one, for sure, a man who seemed as rough and tumble as Dean, wearing women's panties, but yet… it worked. As she had noted before, primary colors were a good look against his skin, and it complemented the lines of his body, hip dents sloping down to hide beneath the fabric.

And then, there was the sight of his dick, half-hard, resting heavily against the fabric.

"It looks very good." She couldn't lie to him, now could she? She also couldn't ignore the strange way her mouth was watering. This was a new development. Maybe she could suffer the loss of a pair of panties, even if they were her favorite…

He watched her, cautiously, as her throat swallowed once or twice, her eyes trained directly at his crotch. It clicked in his brain at that very moment.

"Oh my god, this is a _thing_ for you, isn't it?"

She tried to sound embarrassed or possibly even aghast, but her voice betrayed her distraction. "What, no."

"You look like you could drink an entire gallon of water right now, that's how thirsty you are right now. All from staring at my cock in _your_ panties. Oh my _god._" He laughed, not mockingly, but rather as if he were overwhelmingly pleased with this information. He had intended on this just being a simple joke, but no, now he had to see how far he could push this.

"Shit, Em, maybe we should go shopping for some, make me do a little fashion show for you, if you're gonna look at me like you're gonna - ohh…" Em had moved forward to very gently lick at the tip of his dick, mocking her by peeking above the edge of the panties.

"That's… that's not even fair…" His hips stuttered momentarily as she licked again, placing her hand against his length, rubbing gently. The feel of the soft cotton against him made him shudder out a whispered _fuck_, trying to fight off a whimper when she moved away.

"Alright, well, if you want to give me a fashion show, go ahead. Lemme see. Turn around, I need the full visual." Em motioned with her finger to have him spin, and he did, turning slowly. The visual in the back was almost even better.

They fit just shy of being too tight around his backside, and while he didn't exactly have an ass to write home about, it was still tantalizing in these panties. Em couldn't help herself… it was just inviting.

He jumped the minute her hand slapped hard against a cheek, the stinging against his skin causing a hiss to slip through teeth. How had he lost control of this situation already? This was just going to be a quick joke, but now she's already really into this, and she was way more dressed than he was.

"Hmm. Yeah, these do look good on you. But, I'm not sure… I'm sure there's something else I could see you in." She kissed at the small of his back, snapping at the waist of the panties.

Quickly moving from the bed, she scurried over to her dresser, tearing through her drawer before she found _them_. She had only worn them once, but god, she wanted so desperately to see him in these, it was almost a burning ache in her gut. She wasn't even really aware that she was into this, the sight of him in panties; this wasn't really a thing she ever thought about. And yet she wanted nothing more than to stroke him through the fabric, feel him hard and hot against cotton and silk and lace. It seemed way too lovely an image to quit from her mind now.

She closed the drawer, holding them up on a finger, presenting them to him. "These. I'd like to see you in these." Sure, she'd hate to see him out of those hipsters, they really _did_ suit his body, but her curiosity was clawing at her, and she needed it fulfilled.

He held up the new pair of panties in his hands, balking for a moment. "I'll rip them."

"No, I trust you, you won't. Please?"

He saw the look in her eyes, and how with the feigned innocence in her voice, he knew that this would probably end well for him if he did this. He signed himself up for this mess the minute he put the first pair on, he supposed he had to see this through until the end now.

"Fine. Let me get changed in the bathroom though, don't wanna ruin the whole surprise for you or whatever…" He held the fabric bunched in a fist, clenching it a bit tighter when he saw her smile widen.

"Oh, goodie. One more thing Dean… lose the shirt when you do?" Em asked, dropping some of the false innocence from her voice, biting at the tip of her tongue when she looked at him.

Oh this was getting a bit much. He was wearing a plain black t-shirt and the damn panties, and now she wanted him without the shirt and… and _those_ panties? Oh lord.

"I don't know about that, princess." He felt a hand ghost across his lower stomach, before trailing to brush across the length of his dick, causing a bead of precum to form.

"Please? For me?" Oh she knew _exactly_ what she was doing, the little bitch.

"_Fine._"

He walked into the bathroom, closing the door behind him. She didn't hear much grumbling from him, which was surprising, considering the cut of these panties was much more revealing than the prior pair had been. She couldn't wait. She was getting a little bit of a sick thrill from this, seeing him all flustered and yet aroused by wearing women's underwear.

She knew most of it was because of how into this she apparently was, and she knew it started as a prank, but if she could get him all worked up like this, she wondered how far she could take this. She shifted a bit uncomfortably, knowing that she was definitely worked up, feeling the telltale wetness between her legs.

Once the door opened slowly, she couldn't help but sit up on the bed, waiting to see him. He didn't disappoint.

Sitting low, _very_ low, on his hips, was a pair of entirely black lace bikini cut panties, with a tiny silver bow at the front. His cock, even harder now from the friction of the lace, sat barely contained behind it, and Em would have been lying to herself if she didn't catch her mouth drooling.

"So, whaddya think? Everything you ever dreamed of?"

She nodded blankly, motioning for him to come closer to her.

He barely made it over to the bed before she had her hands resting on his hips, and was licking at him through the lace, from root to tip, nails digging in slightly, resulting in a low moan from above her. She rested her head against his hip, looking up, eyes starting to fog over with lust.

"_Now_ it's everything I've dreamed of. But… hmm… there _is_ something else I'd like to see."

She pulled at his hips, making him get onto the bed with her. She quickly took the hoodie and boxers that she was wearing off, before straddling one of his thighs. She rested her hand over his length, the fabric of the lace still warm and wet from where she licked. She rubbed against him a few times, reveling in how he shifted, causing his thigh to rub against her.

"I'd like to see you cum all over these, to be completely honest with you."

Dean felt his eyes almost roll backwards at her talking filthy to him, which meant that she was in rare form. She usually stayed rather quiet, leading for him to make the first move. This was a beautiful change of pace, and he was so absolutely here for it. He, however, wanted to make sure that she got something out of it more than just voyeuristic appeal.

She couldn't help the gasp when his fingers slid inside her, his thumb hovering above her clit.

"And I'd like to feel you cum around my fingers, how about that?"

She nodded, rubbing at him slowly, not wanting to irritate his skin by being too harsh with the lace, gritting out, "deal," when he moved his thumb to stroke lightly against her clit.

This shouldn't have been as hot as it was, but it felt like there was a fire between them, the way that Em rocked back on his hand, riding his fingers, while rubbing him through the lace of the panties. She laid gentle bites along his collar bone, her teeth snagging against skin when he pulled at her hair roughly, forcing her lips against his as he crooked his fingers forward, making her gasp into his mouth.

He was rewarded with her rubbing against him harder, using every drop he leaked to soften the fabric, to make it glide against his skin easier. They worked almost in tandem, each movement of one's hand resulted in the quickening of the other's, and soon they were panting against the sweat-dampened skin of the other.

He could feel how close she was, his fingers were soaked, and with how insistently she was bucking against his hand, how her thighs were tightening close, it wouldn't take much longer at all.

"That's it Em, that's it baby… Cum for me, baby. Cum for me, and I promise, I'll cum all over these panties for you."

Her hand tightened around his length, her body spasming as she rode his fingers to completion, causing just enough harsh friction against his cock.

With a bit-off oath and eyes clenched shut, he came, groaning out the release as she kept stroking him through it, coating her hand, his cock, and the black lace with his cum.

He pulled his hand away from her, allowing her to slump next to him, gasping for breath, legs still twitching slightly. He groaned again, pulling tenderly at the sticky lace against him.

"That was… different. A good different."

She looked up at him, half a smile on her face. "Something you'd do again?"

A tired laugh huffed out. "If you're cool with it."

"Sure thing. There's a lot of colors and cuts I'd like to see on you…" She was quiet for a moment, kissing at his shoulder. "Oh, and Dean?"

"Yeah babe?"

"You can keep the striped ones. They look better on you anyway."


End file.
